Where to Find the BEST Boys’ Clothes

I absolutely LOVE shopping. But you know what I don’t love? Shopping with my boys. Because not only do they prefer the most flamboyant and cringe worthy color combinations, but I also hate having to keep tabs on their antics while perusing the racks trying to make my dollar stretch a little bit further. So that’s why I have become obsessed with online shopping for them. It’s easy, there are great deals (shipping and returns are now oh so easy) and there are so many great clothing options for boys that most brick and mortar stores just don’t carry. Not going to lie, it takes away the sting of not being able to purchase adorable bows and tulle skirts. So here are my tips on where to find the best boys’ clothes:

Simkin Family Session

Photo by Thomas Kubik of TK Photography

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Why do we love Gymboree so much? Because there is ALWAYS a deal on something (pajamas, jeans, sweaters, etc.) and these clothes LAST. Having two boys so close together in age, my little guy tends to get mostly hand me downs (sorry, little buddy!). I can wash Gymboree clothes over and over again and they still look brand new. We especially love their jeans and cargo pants that can stand up to rough and tumble play.

Wee Rascals

I came across Wee Rascals on Instagram and I’m so glad that I did. Their adorable graphic tees not only pass my boys’ “comfy” tests, but also make them look chic and stylish even if they are running around without pants on (please tell me I’m not the only one who is dealing with boys who prefer to run around in their undies all day?!?). My favorite part is that the tees are inspired by history, so they are a great talking point to teach young minds all about the world around them.

Janie and Jack

Have a special event to attend? Janie and Jack has you covered. People swoon over my boys when I bust out their nautical outfits and bow ties, and I have to admit that I think their selection of boys’ clothes is cuter than their girls’ outfits. Since Janie and Jack tends to run a little bit big, I recommend that you order one size down to ensure a proper fit. Oh, and don’t leave their website without checking out their great selection of hats. To die for.

Loved by Hannah and Eli

I am a very proud “Mama Bear” and I have the graphic tees to prove it. And since my boys are my baby bears, I love getting them “Baby Bear” and “Man Cub” tees. Who said that moms and their sons can’t get in on the #twinning craze?!?


Looking for clothes that are simple and straightforward? Then Primary is the website for you. My oldest son is quite literally obsessed with the color red so he loves the fact that he can pick out tons of simply red pieces of clothing on this website, while I am obsessed with the fact that I can shop for clothing that doesn’t have obnoxious characters or sayings on them.

Half Pint Shop

There isn’t a day that goes by when my boys don’t get compliments on their clothes when they are sporting something new from Half Pint Shop. A stylish Chicago mom, Macaire Douglas, owns the shop and stocks it with outfits that she would dress her own two boys in. Our personal favorites are the hooded sweatshirts…I even love them so much that I buy them in multiple sizes so my boys can wear them for years to come! And be sure to check out the physical store located at 3756 North Ashland Avenue, Chicago.

Boy moms, where are your favorite places to shop for your boys? I’d love to hear about some new spots! And once you are ready to sell outgrown clothes, be sure to check out my favorite consignment shops.

Happy Shopping!
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  1. Rebecca Swenor says

    These all sound like great places to shop for boys. I know my niece was easier to shop for than my boys when we would go school shopping. Thanks for sharing the places to shop.

  2. Lynndee says

    I haven’t tried shopping in any of these stores for my son yet. Thanks for the list. Will check them out. Our son def needs some new fall clothes. He’s growing so fast!

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